Over 16 million children in the U.S. experience poverty, with a disproportionate amount being African American (National Poverty Center, http://www/npc.umich.edu/poverty). These children typically attend schools that lack adequate funding and instructional resources, yield low academic test scores, and have very high teacher and administrator turnover (Gooden, 2012). The lowest performing of these schools are deemed by state and federal governments as high priority reform schools, led by principals charged with significantly improving the test scores within a few years despite daunting structural inequalities that have hampered their schools for long periods of time (Gooden, 2012; McCray, Wright, & Beachum 2007). While many such principals are dedicated and skilled, a growing body of research suggests they lack sufficient professional development and support in their reform roles, which contributes to their burn out, curtailed growth, and/or disillusionment (Peck & Reitzug, 2014; Wilson, 2015). This paper profiles two African American principals in a southeastern, U.S. state who led high priority reform schools. Findings about their experiences are drawn from a subset of data from two larger qualitative interview studies of such principals. Both studies were grounded in the counter-narrative tradition of Critical Race Theory (CRT), which analyzes the perspectives and experiences of those routinely marginalized and silenced (Solórzano & Yosso, 2002; Stovall, 2006). Both principals strove to meet the diverse needs of their students in a manner that reflected ethics of critical care, a sense of ownership of their school, and interconnectedness with their students’ lives and the broader community. This led them to “blow against the wind” as they approached school leadership from a transformative perspective guided by social justice goals that transcended traditional administrative and academic pursuits and disrupted practices they felt were racially and/or socioeconomically biased (Cooper, 2009; Shields, 2012). Their leadership and student advocacy methods clashed with district (or central office) ideals and sometimes official policies. Consequently, each faced severe repercussions for their leadership styles. The authors provide a CRT-driven analysis of the principals’ narratives and school contexts. They highlight the importance of supporting and retaining school leaders who understand and are responsive to the complex, intersecting nuances of race and poverty and their inequitable impact on the U.S. educational system. Strategies for doing so are offered.

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